The Lone Rock to Boscobel 2 day trip (this trip can also be done in 3 days) is a good trip for the semi-fit (there are shorter 2 day trips available). There are some great bluff bluff views along the way and if you camp upriver from Blue River (20ish miles into the trip) you should have no problem finding your own sand bar, even on the busiest Saturday night.
If you're renting 2 or more canoes/kayaks you'll drop people and gear off at the landing and then ONLY the drivers will continue downriver to the WI River Outings shop in Boscobel. They'll then transport the boats and drivers upriver to start your trip. This way, when you finish in Boscobel you can Land-Load-Leave. Victoria Park Landing is roughly halfway through your trip. In high water, if sand bars are limited, this will be your best camping option to be on high/dry ground. It's a short walk into town to a convenient store or grocery store.
While the river is generally shallow, there are drop-offs. Those who are not strong swimmers should always where their life jacket when their feet are wet.
WI River Outings rents: sleeping bags, tents, inflatable sleeping mats, camp tables, camp chairs, seat backs and HIGHLY recommends at least a dry bag.
The river is wide, so shade can be at a premium. If it's windy, it will generally be in your face since you're heading southwest. You'll learn to read the river quickly to avoid submerged sand bars. The most challenging part of the entire trip is making the turn into the Boscobel landing.